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If I'm doing designs with text, do I always have to expand /expand appearance before exporting in PNG? I need it to upload to Print on Demand websites.
No you don't have to expand, png is a raster format it does not keep any of the vector editability of your design in Illustrator.
So keep your Illustrator file unexpanded.
Check if the Print on Demand website supports PDF, it will give you better quality.